New optical materials containing isobenzofuran

Isobenzofuran, a member of the benzo[c]heterocycles, is an extremely reactive molecule with unusual electronic properties. In this thesis we investigate the integration of isobenzofuran subunits into conjugated optical materials. We discuss the properties of isobenzofuran, its role in organic chemistry, and the synthesis of isobenzofuran containing materials in the context of the other well known benzo[c]heterocycle, isothianaphthene. Isothianaphthene has been used in conducting polymers and organic fluorophores as a proquinoid unit, and we posit that isobenzofuran, due to its intrinsic instability, would display greater proquinoid character. To study this effect, we developed a synthetic route to integrate isobenzofuran into near-infrared donor-acceptor type fluorophores. These dyes, the IBF-NIADs, exhibit red-shifted absorption and emission over corresponding isothianaphthene containing dyes, thus highlighting the effective proquinoid nature of isobenzofuran. With the fundamentals of the IBF-NIAD dyes developed, we then expanded the series into a library of fluorophores for near-infrared fluorescence imaging application. Due to low absorption, autofluorescence, and scattering in the near-infrared region, near-infrared fluorescence imaging has the potential to provide non-invasive diagnostic techniques. In particular, our interest lay in imaging P-amyloid plaques, a hallmark pathology of Alzheimer's disease.

Department dc:contributor.department

Massachusetts Institute of Technology. Dept. of Chemistry.

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2009

Author dc:creator

• Meek, Scott Thomas

Advisor dc:contributor.advisor

• Timothy M. Swager.

• Chemistry.

Statement dc:rights

• M.I.T. theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission. See provided URL for inquiries about permission.

Licence dc:rights.uri

• http://dspace.mit.edu/handle/1721.1/7582

Language dc:language.iso

eng

Handle dc:identifier.uri

http://hdl.handle.net/1721.1/49742

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/49742